Boat shoes have come a long way from their start as a solution to slippery decks. Today, they’re a preppy staple topping trend lists everywhere. But how did they make the leap from boat decks to city streets? Scroll down and find out.

You’ve seen these shoes before. You probably even have a pair or two in your closet – or on your feet at this very moment. But can you identify them by name? If not, then no worries. We’re here to break it down for you.

Now that you know what they are, here are a few tips on how to wear them.

Boat Shoes: Whether you’re keeping steady on a sloop or trekking through an urban jungle, boat shoes are the go-to casual shoe. Ditch the socks and wear them with shorts when the temps start to rise or pair them with khakis or jeans all through winter.

Penny Loafers: Easily dressed up or down, you can pair your penny loafers with everything from jeans and a polo (roll up the cuffs and go sockless if you’re feeling daring) to chinos, a button-front, and a blazer.

Chukkas: Often done up in leather or suede, these flat turf boots have a laid-back, yet very put-together, vibe. Mix up your look with slim denim and a plaid shirt. Then go ahead and top it all off with a cashmere sweater for that extra dose of polish.

Unfortunately, not every summer soiree includes an easy exit. Sometimes, you have to stick it out – rain, shine, or impossible humidity. So before you head to that next dinner party, take a few hot-summer cues from us.

For Men
It’s hot and muggy out, and you’re going to sweat. Wear a T-shirt, right? Wrong. The Art of Manliness implores you to choose a button-front or polo on sunny days before reaching for the tee. Even a long-sleeve button-front (made of natural fibers) will keep you cooler than a cotton-blend or polyester tee. Not to mention the versatility factor. You’ll seldom feel underdressed.

For occasions that call for a sport coat, wear light colors and fabrics (like white and linen). Heading to a patio or beach-front party? Roll up those pant cuffs and swap out oxfords for boat shoes.

For WomenWe’ll admit it – women sweat, too. (Guys, deal with it). A few things to avoid when hitting the party circuit: cap sleeves, too-short shorts, doing your hair, and the color gray. Go with a billowy off-the-shoulder dress. You’ll stay cool while still showing a little skin. Since you’ll have to bring a bag for those touch-up essentials, make it a big, bright one that’s still slim enough to tuck under your arm.

For Kids
Shorts, tees, stripes, anchors. It’s hard to make them not look cute. Heading to a kid-friendly party? Make sure they’re comfortable – or you’re in for an early night. And don’t forget hats. Even if it’s not an outside event, they’ll probably end up in the yard anyway.

For Home
Not unlike your wardrobe, your summer bed requires cool cotton and linen fabrics for maximum comfort on humid nights. Satin and silk may sound appealing, but they’re not as breathable. Swap your heavy winter comforter for a lightweight duvet in a creamy white or nude hue.